Phenol oxidation. Part II. Synthesis of orientalinone, corydine, and isocorytuberine
作者:A. H. Jackson、J. A. Martin
DOI:10.1039/j39660002222
日期:——
Ferricyanide oxidation of 1,2,3,4-tetrahydro-7-hydroxy-1-(2-hydroxy-4,5-dimethoxybenzyl)-6-methoxy-2-methyl-isoquinoline afforded a mixture of two dienones in 26% yield. Borohydride reduction of one of these gave the corresponding dienol which rearranged in acidic media to give either orientalinone, corydine, or isocorytuberine depending on the conditions used.
1,2,3,4-四氢-7-羟基-1-(2-羟基-4,5-二甲氧基苄基)-6-甲氧基-2-甲基-异喹啉的铁氰化物氧化制得两种二烯酮的混合物,收率26% 。其中之一的硼氢化物还原得到相应的二烯醇,其在酸性介质中重排,从而根据所使用的条件得到东方三烯酮,可待因或异亮氨酸。